(S)-2-acetoxypropanol | 153904-73-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-acetoxypropanol
• 英文别名: [(2S)-1-hydroxypropan-2-yl] acetate
• CAS: 153904-73-5
• 化学式: C₅H₁₀O₃
• 分子量: 118.133
• InChiKey: YJNKLTDJZSXVHQ-BYPYZUCNSA-N

物化性质

• 沸点：
  191.0±13.0 °C(Predicted)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-acetoxypropanol 在 C₅H₁₁ONa 作用下， 以 戊醇 为溶剂， 以98%的产率得到S-环氧丙烷
  参考文献：
  名称：

  Cotterill, Ann S.; Gill, Melvyn; Milanovic, Nives M., Journal of the Chemical Society. Perkin transactions I, 1995, # 10, p. 1215 - 1224

  摘要：

  DOI：
• 作为产物：
  描述：

  过氧化乙酰丙酮 在 baker's yeast 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 (S)-1-acetoxy-2-propanol 、 (S)-2-acetoxypropanol
  参考文献：
  名称：

  The baker's yeast reduction of 1-acetoxy-2-alkanones in the presence of a sulfur compound

  摘要：

  Improved enantioselectivity was achieved in the baker's yeast reduction of the 1-acetoxy-2-alkanone derivatives by the addition of a sulfur compound such as L-cysteine and phenyl vinyl sulfide. The reaction rate of the baker's yeast reduction was accelerated using a sulfur compound as an additive. The migration of the acetyl group and the hydrolysis of the acetoxy group of the substrate was suppressed using a sulfur compound. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00434-5

文献信息

• Tunable <i>P</i>-Chiral Bisdihydrobenzooxaphosphole Ligands for Enantioselective Hydroformylation
  作者：Renchang Tan、Xin Zheng、Bo Qu、C. Avery Sader、Keith R. Fandrick、Chris H. Senanayake、Xumu Zhang

  DOI：10.1021/acs.orglett.6b01452

  日期：2016.7.15

  Air-stable and tunable chiral bisdihydrobenzooxaphosphole ligands (BIBOPs) were employed in rhodium-catalyzed asymmetric hydroformylation of various terminal olefins with excellent conversions (>99%), moderate-to-excellent enantioselectivities (up to 95:5 er), and branched to linear ratios (b:l) of up to 400.

  空气稳定且可调的手性双二氢苯并恶唑磷配体（BIBOP）用于铑催化的各种末端烯烃的不对称加氢甲酰化反应，具有出色的转化率（> 99％），中等至优异的对映选择性（高达95：5 er），并分支为线性比（b：l）高达400。
• Challenging the absence of observable hydrogens in the assignment of absolute configurations by NMR: application to chiral primary alcohols
  作者：Félix Freire、José Manuel Seco、Emilio Quiñoá、Ricardo Riguera

  DOI：10.1039/b617184b

  日期：——

  The absolute configuration of beta-chiral primary alcohols devoid of observable hydrogens on one of the beta-substituents at the asymmetric carbon (L(1)/L(2)) can be determined by comparison of the (1)H NMR of their (R)- and (S)-9-AMA ester derivatives and analysis of the Deltadelta(RS) for the L substituent and the Cbeta-H.

  β-手性伯醇的绝对构型在不对称碳（L（1）/ L（2））的β-取代基之一上没有可观察到的氢，可以通过比较它们的（1）H NMR来确定R）-和（S）-9-AMA酯衍生物以及L取代基和Cbeta-H的Deltadelta（RS）分析。
• Highly efficient enzymatic asymmetric reduction by use of regenerating NADPH in bakers' yeast cell-free extract
  作者：Kohji Ishihara、Takashi Sakai、Sadao Tsuboi、Masanori Utaka

  DOI：10.1016/s0040-4039(00)60730-x

  日期：1994.6

  Bakers' yeast cell-free extract was found to reduce 1-acetoxy-2-alkanones to (S)-1-acetoxy-Z-alkanols in 59 - 88% yield and 95 - >99% ee by use of a catalytic amount of NADPH with glucose as a hydride source and without addition of any enzyme for the cofactor regeneration.
• Breeden, Simon; Cole-Hamilton, David J.; Foster, Douglas F., Angewandte Chemie - International Edition, 2000, vol. 39, # 22, p. 4106 - 4108
  作者：Breeden, Simon、Cole-Hamilton, David J.、Foster, Douglas F.、Schwarz, Gary J.、Wills, Martin

  DOI：——

  日期：——